CN101050205A - Compound containing cation radical of piperazidine, synthetic method, and application - Google Patents
Compound containing cation radical of piperazidine, synthetic method, and application Download PDFInfo
- Publication number
- CN101050205A CN101050205A CNA2007100521761A CN200710052176A CN101050205A CN 101050205 A CN101050205 A CN 101050205A CN A2007100521761 A CNA2007100521761 A CN A2007100521761A CN 200710052176 A CN200710052176 A CN 200710052176A CN 101050205 A CN101050205 A CN 101050205A
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- Prior art keywords
- piperazine
- compound
- alkane
- alkyl
- reaction
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2020/00—Specified physical or chemical properties or characteristics, i.e. function, of component of lubricating compositions
- C10N2020/01—Physico-chemical properties
- C10N2020/077—Ionic Liquids
Abstract
This invention relates to a method for synthesizing a compound containing piperazine cation group and its application. The structural formula of the compound is shown, wherein, R1, R2, R3 and R4 are C1-C8 alkyl, and X- is Br-, Cl-, BF4- or PH6-. The compound has excellent properties of ionic liquid, and can dissolve a variety of poorly soluble compounds. The method has such advantages as low cost, simple synthesis, and high yield, and is suitable for mass production. The compound as ionic liquid can be used as gas absorbent and liquid extraction phase in separation engineering, reaction medium and catalyst in chemical reactions, electrolyte (including ion-conducting polyelectrolyte) in electrochemistry, cellulose solvent, multifunctional lubricant, matrix for mass spectrometry, and chromatographic stationary phase.
Description
Technical field
The present invention relates to contain the compound and the preparation method and use thereof of cation radical of piperazidine, belong to the technical field of organic chemical reactions method.
Background technology
Ionic liquid (ionic liquids) is called ionic liquid at room temperature (room temperature ionic liquid), room temperature melting salt (room temperature molten salts), organic ion liquid etc. again, be called for short RTILs, only be meant and form in room temperature or or near being the salt of liquid under the room temperature by ion.Only have zwitterion in the ionic liquid, do not have neutral molecule, its principal feature is that positively charged ion is bigger and asymmetric, and negatively charged ion is less.The ionic liquid of current research can be divided into by positively charged ion: the quaternary ammonium alkyl ion; The alkyl quaternary phosphonium ion; 1, the imidazole-like ionic that the 3-dialkyl group replaces; The pyridinium ion that the N-alkyl replaces.Divide and to be divided into by negatively charged ion: metal species (as: AlCl
4 -, CuC
2 -Deng) and non-metal kind (as: BF
4 -, PF
6 -, NO
3 -, SbF
6 -, ClO
4 -, CF
3SO
3 -, C
3F
7COO
-, C
4F
9SO
3 -, CF
3COO
-Deng).Can be divided into by Lewis acidity: the ionic liquid of adjustable acid-basicity is (as AlC
4 -) and the neutral ionic liquid (as BF
4 -, PF
6 -, NO
3 -, SbF
6 -, ClO
4 -Deng).Wherein 1, the imidazole salt that the 3-dialkyl group replaces is ion liquid synthetic and applied research gets the most deeply and extensively.
Ionic liquid does not almost have vapour pressure; Thermally-stabilised good (reaching as high as 300～400 ℃); Has good electrical conductivity; To organic compound, mineral compound, organometallics, gas (H
2, CO, O
2Deng) solvability widely arranged; Also can be with organic solvent, water is miscible or insoluble formation homogeneous phase, two-phase or multiphase reaction system; The most attractive is its polarity, hydrophilic, close ester can be by changing alkyl carbon chain length with select different negative ions to regulate, therefore the programmable solvent that is otherwise known as, these characteristics make ionic liquid become to have concurrently " solid " liquid (solidliquid) of liquid and solid function and characteristic.Ionic liquid has obtained widespread use as new green solvent in research fields such as organic synthesis, novel material, electrochemistry.The main application has: 1, be used for various chemical reactions as green solvent, replace volatile organic solvent, be easy to separate, reduce environmental pollution; 2, as the carrier of catalyzer or various catalyzer, improve catalytic efficiency, reduce catalyst consumption; 3, improve Activity of Chemical Reaction and selectivity, shorten the reaction times, reduce energy consumption; 4, as electrochemical material such as liquid electrolyte etc.But above-mentioned common a few class ionic liquids are because the raw materials cost height, complex synthetic route, and productive rate is low etc., and reason has limited its suitability for industrialized production and application.
Piperazine and N-alkylpiperazine are the nitrogenous heteroatomic ring compound of a class.As tertiary amine compound, piperazine and N-alkylpiperazine can generate quaternary ammonium salt with halohydrocarbons reaction obviously, again by anionresin, can obtain a series of quaternary ammonium salts that contain different anions.Some piperazine quaternary ammonium salt is liquid at normal temperatures, and the fusing point of some piperazine quaternary ammonium salt is at 40～70 ℃.This has just constituted the ion liquid compound that a class contains cation radical of piperazidine.
It is simple to have not yet to see synthetic route, and productive rate is higher, the report of the fluid cpds that contains cation radical of piperazidine with low cost.Therefore the cation radical of piperazidine ionic liquid of developing a class production cost low (cost of material piperazine and N-alkylpiperazine are lower than N-alkyl imidazole), synthetic route simple (adopting the one kettle way reaction), productive rate higher (overall yield＞90%) is the industrialized key of present ionic liquid.
Summary of the invention
The object of the present invention is to provide the compound and the preparation method and use thereof that contain cation radical of piperazidine, the gained compound compares with existing ionic liquid that to have synthetic route simple, advantage such as productive rate is higher, and is with low cost, and character is good.
The contriver obtains following formula (1) X by chloro or bromo alkane and piperazine and the reaction of N-alkylpiperazine
-Be Br
-, Cl
-The compound that contains the piperazine group, gained compound and NH
4BF
4Or NH
4PF
6Carry out ion-exchange and obtain following formula (1) X
-Be BF
4 -Or PF
6 -The compound that contains the piperazine group.
The compound that contains the piperazine group of the present invention is represented with following general formula (1):
R
1, R
2, R
3, R
4Be respectively C
2～C
8Alkyl, R
1, R
2, R
3, R
4Can be identical alkyl and also can be different alkyl; X
-Be bromine or cl anion and BF
4 -, PF
6 -
Above-mentioned C
2～C
8Alkyl is meant ethyl, alkyl such as propyl group, sec.-propyl, isobutyl-, amyl group, isopentyl, hexyl, isohexyl, heptyl, different heptyl, octyl group or iso-octyl; X
-Be meant chlorine, bromine anions, BF
4 -Or PF
6 -
Preferred The compounds of this invention is R wherein
1, R
2, R
3, R
4Be selected from C respectively alone
2, C
4, C
6Or C
8Alkyl, X
-Formula (1) compound for bromine anions.
Preferred The compounds of this invention also is R wherein
1, R
2, R
3, R
4Be selected from ethyl, butyl, hexyl or octyl group, X respectively alone
-Be BF
4 -Or PF
6 -Formula (1) compound.
The present invention also provides above-mentioned formula (1) to contain the synthetic method of the compound of piperazine group: 1. press piperazine or N-alkylpiperazine and bromo C
2～C
8Alkane or chloro C
2～C
8The alkane mol ratio is 1: 4～20 ratio, adds bromo C in piperazine or N-alkylpiperazine
2～C
8Alkane or chloro C
2～C
8Alkane, with methyl alcohol, ethanol, propyl alcohol, Virahol or N, dinethylformamide is a solvent, at 50～150 ℃, 1～10 normal atmosphere reacted 10～200 hours down; Can obtain formula (1) X after reaction product is purified
-Be Br
-Or Cl
-The compound that contains the piperazine group.
2. N is pressed, N-C in the reaction of being carried out in 1. in the step back (chromatogram detection) that finishes
2～C
8Alkyl-N ', N '-C
2～C
8Alkyl-piperazine chlorination or brometo de amonio and NH
4BF
4Or NH
4PF
6Mol ratio is 1: 2～10 ratio, at N, and N-C
2～C
8Alkyl-N ', N '-C
2～C
8Alkyl-piperazine chlorination or brometo de amonio (are the above-mentioned formula that obtains (1) X
-Be Br
-, Cl
-The compound that contains the piperazine group) in add NH
4BF
4Or NH
4PF
6,, reacted 10～200 hours at 20～50 ℃; Obtain X after reaction product is purified
-Be BF
4 -Or PF
6 -The compound that contains the piperazine group.
The contriver finds that The compounds of this invention is good green solvent, can dissolve many very difficult dissolved compounds, and solvency power is stronger than organic solvent commonly used.
The contriver finds that also the synthetic route of The compounds of this invention is simple, and productive rate is higher, and is with low cost; Be fit to large-scale industrial production.
The compounds of this invention has as the applicable field of ionic liquid: make gas absorbent and liquid extraction mutually in separation engineering; In chemical reaction, make reaction medium sometimes simultaneously as catalyzer; In electrochemistry as ionogen (comprise make ionic conduction polymer electrolyte); Also may be used for other aspects such as dissolving cellulos, as omnipotent lubricant, as mass spectral matrix, equate as chromatographic stationary.
The toxicity that the inventor goes back discoverable type (1) compound is lower, and biological degradation is good, to environment gentleness, pollution-free.
Embodiment
With R in the above-mentioned formula (1)
1, R
2, R
3And R
4Be butyl, X
-For the anionic The compounds of this invention of fluoroboric acid root is that the synthetic method of example may further comprise the steps:
A, add bromination of n-butane (piperazine and bromination of n-butane mol ratio are 1: 6) in piperazine, solvent can be methyl alcohol, ethanol, propyl alcohol, Virahol, N, dinethylformamide etc., reacting by heating, temperature of reaction is 80 ℃, and pressure is the 1-10 normal atmosphere, and the reaction times is 10-200 hour.
B, the reaction back (chromatogram detections) that finishes adds ammonium borofluoride (N ', the N '-tetrabutyl-piperazine brometo de amonio and ammonium borofluoride mol ratio are 1: 2～6 for N, N) in above-mentioned reaction solution, temperature of reaction is 30 ℃, and the reaction times is individual hour of 10-200.Obtain N after reaction product is purified, N, N ', N '-tetrabutyl piperazine ammonium borofluoride.
Same R
1, R
2, R
43, R
4Be C
2～C
8Alkyl, X is bromine or cl anion and BF
4 -, PF
6 -Formula of the present invention (1) compound can be according to the preparation of above-mentioned method.
The following examples can make those skilled in the art more fully understand the present invention, but do not limit the present invention in any way.
Embodiment one
N, N, N ', N '-tetraethyl--piperazine brometo de amonio
Piperazine 8.6 grams, monobromethane 100 grams and solvent methanol 150 are restrained in reaction unit, and temperature of reaction is 50 ℃, and pressure is 4 normal atmosphere, and the reaction times is 200 hours, after reaction finishes (chromatogram detection), boils off solvent.Can obtain N after reaction product is purified, N, N ', the N '-tetrabutyl-piperazine brometo de amonio, to air-stable, productive rate 93%.
m.p.：50℃
High resolution mass spectrum: [M-Br]
+=200
1HNMR(D
2O，δ/ppm?relative?to?TMS)：3.625(t，8H)，3.281(t，8H)，1.251(t，12H)。
Embodiment two
N, N, N ', N '-four isobutyl-s-piperazine ammonium chloride
Piperazine 8.6 grams, Sec-Butyl Chloride 180 grams and etoh solvent 150 are restrained in reaction unit, and temperature of reaction is 80 ℃, and pressure is 1 normal atmosphere, and the reaction times is 100 hours, after reaction finishes (chromatogram detection), boils off solvent.Can obtain N after reaction product is purified, N, N ', the N '-tetrabutyl-piperazine ammonium chloride, to air-stable, productive rate 94%.
m.p.：56℃
High resolution mass spectrum: [M-Cl]
+=312
1HNMR(D
2O，δ/ppm?relative?to?TMS)：3.332(m，4H)，3.615-3.618(s，8H)，1.714(m，8H)，1.332(t，12H)，0.964(t，12H)。
Embodiment three
N, N, N ', N '-four isohexyls-piperazine ammonium borofluoride
Piperazine 8.6 grams, 2-bromohexane 90 grams and solvent propyl alcohol 150 are restrained in reaction unit, and temperature of reaction is 130 ℃, and pressure is 5 normal atmosphere, reaction times is 100 hours, after reaction finishes (chromatogram detection), adds ammonium borofluoride 30 grams in above-mentioned reaction solution, temperature of reaction is 50 ℃, and the reaction times is 10 hours, after reaction finishes, can obtain N after reaction product is purified, N, N ', N '-four isohexyls-piperazine ammonium borofluoride, air, water are stablized productive rate 95%.
m.p.：-10℃
Electrochemical window: 3.8V
Specific conductivity: 3.64 * 10
-3S/cm
Density: 1.45g/ml
High resolution mass spectrum: [M-BF
4]
+=424
1HNMR(D
2O，δ/ppm?relative?to?TMS)：3.745-3.748(m，4H)，3.662-3.666(s，8H)，1.614-1.642(m，8H)，1.25(t，28H)，0.960-0.97(t，12H)。
Embodiment four
N, N, N ', N '-four octyl groups-piperazine hexafluorophosphoric acid ammonium
N-methyl-piperazine 8.6 grams, bromooctane 150 grams and solvent DMF 150 are restrained in reaction unit, and temperature of reaction is 150 ℃, and pressure is 6 normal atmosphere, reaction times is 150 hours, after reaction finishes (chromatogram detection), adds hexafluorophosphoric acid ammonium 30 grams in above-mentioned reaction solution, temperature of reaction is 40 ℃, and the reaction times is 25 hours, after reaction finishes, can obtain N after reaction product is purified, N, N ', N '-four octyl groups-piperazine hexafluorophosphoric acid ammonium, air, water are stablized productive rate 92%.
m.p.：-6℃
Electrochemical window: 3.6V
Specific conductivity: 5.47 * 10
-3S/cm
Density: 1.12g/ml
High resolution mass spectrum: [M-PF
6]
+=537
1HNMR(D
2O，δ/ppm?relative?to?TMS)：3.615-3.618(s，8H)，3.282(t，8H)，1.714(m，8H)，1.253～1.333(t，40H)，0.965(t，12H)。
Embodiment five
N, N '-diethyl-N, N '-dioctyl-piperazine hexafluorophosphoric acid ammonium
With N, N '-ethyl-piperazine 10 grams, bromooctane 100 grams, 100 gram acetonitriles are in reaction unit, and temperature of reaction is 90 ℃, pressure is 2 normal atmosphere, reaction times is 200 hours, after reaction finishes (chromatogram detection), adds hexafluorophosphoric acid ammonium 30 grams in above-mentioned reaction solution, 35 ℃ were reacted 50 hours, can obtain N after reaction product is purified, N '-diethyl-N, N '-dioctyl-piperazine hexafluorophosphoric acid ammonium, air, water are stablized productive rate 95%.
m.p.：-5℃
Electrochemical window: 3.9V
Specific conductivity: 3.37 * 10
-3S/cm
Density: 1.14g/ml
High resolution mass spectrum: [M-PF
6]
+=368
1HNMR(D
2O，δ/ppm?relative?to?TMS)：3.615-3.618(s，8H)，3.282(t，8H)，1.714(m，4H)，1.253～1.333(t，26H)，0.965(t，6H)。
Embodiment six
N, N, N ', the N '-tetraethyl--application of piperazine ammonium borofluoride in synthesis of caprolactam
At N, N, N ', in the catalytic media of N '-tetraethyl--piperazine ammonium borofluoride and P contained compound, under 40-60 ℃ of temperature, the Beckmann rearrangement reaction can take place and generate hexanolactam in cyclohexanone-oxime, can obtain fabulous transformation efficiency (100%) and selectivity (90%), after reaction finished, product was by after the extracted with diethyl ether, and ionic liquid can recycling use.
Embodiment seven
N, N, N ', the application of N '-four octyl groups-piperazine ammonium borofluoride in synthetic propylidene glycerine
Get glycerine 9.2 grams, N, N, N ', N '-four octyl groups-piperazine ammonium borofluoride 10 grams, acetone 50 grams, 100 gram sherwood oils are as the band aqua, and reflux was reacted 10 hours, boil off solvent, can obtain propylidene glycerine 12 grams through handling, productive rate 91%, ionic liquid is recyclable to be recycled.
Claims (9)
1. the compound that contains cation radical of piperazidine, its structural formula is:
R in the formula
1, R
2, R
3, R
4Be respectively C
2～C
8Alkyl; X
-Be bromine anions, cl anion, BF
4 -Or PF
6 -
2. according to the described compound of claim 1, it is characterized in that: R
1, R
2, R
3, R
4Be selected from ethyl, propyl group, sec.-propyl, isobutyl-, amyl group, isopentyl, hexyl, isohexyl, heptyl, different heptyl, octyl group or iso-octyl respectively.
3. according to the described compound of claim 2, it is characterized in that: X
-Be bromine anions.
4. according to the described compound of claim 2, it is characterized in that: X
-Be BF
4 -, PF
6 -
5. according to claim 1 or 2 or 3 or 4 described compounds, it is characterized in that: R
1, R
2, R
3And R
4Be butyl.
6. according to claim 1 or 2 or 3 or 4 described compounds, it is characterized in that: R
1And R
3Be ethyl, R
2And R
4Be butyl.
7. the synthetic method of the described compound of claim 1 is characterized in that: press piperazine, N-alkylpiperazine or Piperazine anhydrous and bromo C
2～C
8Alkane or chloro C
2～C
8The alkane mol ratio is 1: 4～20 ratio, adds bromo C in piperazine, N-alkylpiperazine or Piperazine anhydrous
2～C
8Alkane or chloro C
2～C
8Alkane, with methyl alcohol, ethanol, propyl alcohol, Virahol or N, dinethylformamide is a solvent, at 50～150 ℃, 1～10 normal atmosphere reacted 10～200 hours down; The purified described X of claim 1 that promptly obtains of product
-Be Br
-Or Cl
-The compound that contains cation radical of piperazidine.
8. the synthetic method of the described compound of claim 1 is characterized in that: 1. press piperazine, N-alkylpiperazine or Piperazine anhydrous and bromo C
2～C
8Alkane or chloro C
2～C
8The alkane mol ratio is 1: 4～20 ratio, adds bromo C in piperazine, N-alkylpiperazine or Piperazine anhydrous
2～C
8Alkane or chloro C
2～C
8Alkane, with methyl alcohol, ethanol, propyl alcohol, Virahol or N, dinethylformamide is a solvent, at 50～150 ℃, 1～10 normal atmosphere reaction down obtained N, N-C in 10～200 hours
2～C
8Alkyl-N ', N '-C
2～C
8Alkyl-piperazine chlorination, brometo de amonio compound; 2. in step product 1., press N, N-C
2～C
8Alkyl-N ', N '-C
2～C
8Alkyl-piperazine chlorination, brometo de amonio compound and NH
4BF
4Or NH
4PF
6Mol ratio be that 1: 2～5 ratio adds NH
4BF
4Or NH
4PF
6,, react and carried out anionresin in 10～200 hours at 20～50 ℃; Obtain X after product is purified
-Be BF
4 -Or PF
6 -The compound that contains the piperazine group.
9. the described compound of claim 1 is as ion liquid purposes.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNA2007100521761A CN101050205A (en) | 2007-05-15 | 2007-05-15 | Compound containing cation radical of piperazidine, synthetic method, and application |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNA2007100521761A CN101050205A (en) | 2007-05-15 | 2007-05-15 | Compound containing cation radical of piperazidine, synthetic method, and application |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN101050205A true CN101050205A (en) | 2007-10-10 |
Family
ID=38781829
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CNA2007100521761A Pending CN101050205A (en) | 2007-05-15 | 2007-05-15 | Compound containing cation radical of piperazidine, synthetic method, and application |
Country Status (1)
| Country | Link |
|---|---|
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|---|---|---|---|---|
| CN102250039A (en) * | 2011-05-16 | 2011-11-23 | 浙江大学 | Ionic liquid of N-methyl piperazine salt and preparation method thereof |
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| CN102952097A (en) * | 2011-08-30 | 2013-03-06 | 海洋王照明科技股份有限公司 | Double-centre piperazine ionic liquid, and preparation method and application thereof |
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| CN103896876A (en) * | 2012-12-28 | 2014-07-02 | 海洋王照明科技股份有限公司 | Double-center piperazine ionic liquid, preparation method thereof, electrolyte and lithium-ion battery |
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| CN102791675A (en) * | 2009-11-06 | 2012-11-21 | 陶氏环球技术有限责任公司 | Difunctional, amine-based surfactants, and their precursors, preparation, compositions and use |
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| CN102250039A (en) * | 2011-05-16 | 2011-11-23 | 浙江大学 | Ionic liquid of N-methyl piperazine salt and preparation method thereof |
| CN102952097B (en) * | 2011-08-30 | 2015-01-07 | 海洋王照明科技股份有限公司 | Double-centre piperazine ionic liquid, and preparation method and application thereof |
| CN102952097A (en) * | 2011-08-30 | 2013-03-06 | 海洋王照明科技股份有限公司 | Double-centre piperazine ionic liquid, and preparation method and application thereof |
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| CN102898317B (en) * | 2012-10-12 | 2015-04-22 | 四川农业大学 | Organic amino compounds serving as immunopotentiators, metabolic enhancers or roborants and preparation method and use thereof |
| CN103896876A (en) * | 2012-12-28 | 2014-07-02 | 海洋王照明科技股份有限公司 | Double-center piperazine ionic liquid, preparation method thereof, electrolyte and lithium-ion battery |
| CN103772300A (en) * | 2013-12-31 | 2014-05-07 | 浙江大学 | 1-ethyl-4-alkylpiperazine ionic liquid and preparation method and application thereof |
| CN103709123A (en) * | 2013-12-31 | 2014-04-09 | 浙江大学 | 1, 4-dimethyl-1-alkyl piperazine ionic liquid as well as preparation method and applications thereof |
| CN103772300B (en) * | 2013-12-31 | 2015-04-29 | 浙江大学 | 1-ethyl-4-alkylpiperazine ionic liquid and preparation method and application thereof |
| CN103709123B (en) * | 2013-12-31 | 2015-05-20 | 浙江大学 | 1, 4-dimethyl-1-alkyl piperazine ionic liquid as well as preparation method and applications thereof |
| CN104174276A (en) * | 2014-08-18 | 2014-12-03 | 南京信息工程大学 | Compounded ionic liquid and synthesis method and application thereof |
| CN104174276B (en) * | 2014-08-18 | 2016-06-29 | 南京信息工程大学 | A kind of compound ionic liquid and synthetic method thereof and application |
| CN105449276A (en) * | 2015-12-25 | 2016-03-30 | 中南大学 | Piperazine ionic liquid electrolyte of lithium ion battery |
| CN105449276B (en) * | 2015-12-25 | 2018-07-17 | 中南大学 | A kind of piperazine ionic liquid lithium-ion battery electrolytes |
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